Classifications

• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
  • C09B55/00—Azomethine dyes
  • C09B55/005—Disazomethine dyes
  • C09B55/007—Disazomethine dyes containing only carbocyclic rings
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
  • C08K5/00—Use of organic ingredients
  • C08K5/0091—Complexes with metal-heteroatom-bonds
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/13—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using azomethine dyes

Definitions

• New compounds have been found which have the general formula (I) ##STR2## in which each R stands for a halogen atom, such as fluorine, chlorine and bromine, a lower alkyl, lower alkoxy group, phenoxy group optionally substituted by 1 or 2 substituents selected from halogen atoms, such as chlorine, lower alkyl and lower alkoxy groups, or is hydroxy, cyano, trifluoromethyl, carboxy, carboxylic acid lower alkyl ester or lower alkanoyl group, or benzoyl optionally substituted by 1 or 2 substituents selected from halogen atoms, such as chlorine, lower alkyl and lower alkoxy groups, n is 1, 2 or 3, preferably 1 or 2, the 1 to 3 radicals R in the nucleus a being identical or different, and each Z stands for hydrogen or halogen, such as bromine or chlorine, lower alkoxy, nitro or cyano.
• each R stands for a halogen atom, such as fluorine, chlorine
• lower in this context is meant to be “1 to 5 carbon atoms in the alkyl moiety”.
• halogen atoms such as chlorine or bromine
• alkyl or alkoxy groups of 1 to 3 carbon atoms trifluoromethyl
• hydroxy, carboxy or carboxylic acid alkyl ester groups having alkyl radicals of 1 to 4 carbon atoms
• each Z stands for a hydrogen atom or bromine atom or a methoxy group
• the new compounds can be obtained according to a process of the invention by condensing 2 mols of an aldehyde of the formula (II) ##STR4## in which Z is defined as above, with 1 mol of a diamine of the formula (III) ##STR5## in which R and n are defined as above, and metallizing the disazo methine compound so obtained simultaneously or afterwards. If desired, mixtures of compounds of the formula (III) can also be used in the condensation reaction.
• the compounds of the formula (I) can also be obtained by reducing an o-nitraniline of the general formula (IV) ##STR6## in which R and n are defined as above, according to usual methods, reacting the o-phenylene diamine obtained without intermediate isolation with the 2-hydroxy-1-naphthaldehyde and metallizing the disazomethine compound.
• Suitable aldehydes of the formula (II) are especially those in which Z is a hydrogen atom, a chlorine or a bromine atom, a methoxy, ethoxy or propoxy group, a nitro or a cyano group. They can be obtained in known manner by formylating the corresponding 2-hydroxynaphthalenes, for example according to the method of Duff.
• Suitable diamines of the formula (III) are especially those in which the benzene nucleus is substituted by at least one halogen atom, for example one or two chlorine or bromine atoms, one or two lower alkyl groups having 1 to 4 carbon atoms, such as methyl, ethyl, propyl or butyl groups, one or two lower alkoxy groups of 1 to 4 carbon atoms, such as methoxy ethoxy, propoxy or butoxy groups, a phenoxy group which may be substituted by halogen atoms, lower alkyl or alkoxy groups, a hydroxy group, a cyano group, a trifluoromethyl group, a carboxy or a carboxylic acid lower alkyl ester group, such as a methyl, ethyl, propyl or butyl carboxylic acid ester group.
• halogen atom for example one or two chlorine or bromine atoms, one or two lower alkyl groups having 1 to 4 carbon atom
• the aldehyde is condensed with the diamine advantageously in water or in an organic solvent at elevated temperature, preferably between about 60° C and the boiling point of the solvent used.
• Suitable solvents are, especially: water, ethanol, glacial acetic acid, dimethyl formamide, N-methylpyrrolidone, glycol mono or dimethyl ether, xylene or mixtures of these solvents.
• the new disazo methine compounds are sparingly soluble in the solvents mentioned and can, therefore, easily be isolated by filtration. Impurities, if ever, can be eliminated by washing them out.
• the disazo methine compounds are converted into their nickel complex compounds by treating them with agents yielding bivalent nickel, for example with a salt of nickel.
• the nickel formiates or acetates are preferably used.
• the metallization is advantageously performed in one of the above-mentioned solvents or in a mixture of these solvents.
• the metallization can also be effected prior to or at the same time as the azomethine condensation by condensing the aldehyde alone or together with the diamine in one of the above-mentioned solvents or in a mixture of these solvents in the presence of nickel salts.
• the new compounds turned out to be very good dyestuffs and are especially good pigments, especially after a finish processing as usual, for example for dyeing masses of synthetic material, which are, in the context, masses of synthetic material or synthetic resins free of or containing solvents and free of or containing plasticizers, for pigmenting paints on oily or aqueous basis and lacquers of most different types, for spin dyeing viscose and cellulose acetate or for pigmenting polyethylene, polystyrene, polyvinyl chloride, caoutchouc and synthetic leather. They are, however, especially suitable for the preparation of metal effect lacquers
• the dyeings obtained have an excellent fastness to migration, light, weather and to solvents, an excellent heat stability and they are distinguished by a high color intensity, high tinctorial strength, a good transparency and, frequently, a high degree of purity of the shades. They also have a good fastness to over-varnishing, to bleeding and a good dispersibility.
• the compounds of the invention are distinguished by a better fastness to migration and to solvents, for example an improved fastness to bleeding and to overvarnishing, an improved transparency and dispersibility and, especially, a higher color intensity and a purer shade.
• the finely dispersed suspension so obtained of the 2-hydroxy-1-naphthaldehyde-nickel complex was introduced into a three-neck flask (reflux cooler, stirrer, thermometer) and heated evenly to 95° C during 2 hours after the addition of 18.3 parts of 4-methyl-o-phenylene diamine.
• the pH value was thus lowered from 7.8 to about 4.
• a solution of 48 parts of sodium acetate in 150 parts of water was added and stirred for 150 minutes at the boiling point, the solution was filtered while hot, washed with 4,000 parts of water and dried.
• Example 12 The metallization according to Example 12 yielded 49 parts (95.1% of the theoretical amount) of a red brown pigment which had the same properties as that described in Example 6.
• Example 23 When in Example 23 the mixture of the methyl-o-phenylene diamines is replaced by corresponding amounts of the diamines of the formula ##STR33## listed in Table 3, and the process is carried out in the manner indicated above, further pigments of the general formula I were obtained according to the invention, in the yields and shades compiled in the following Table 3:

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Textile Engineering (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Paints Or Removers (AREA)
• Coloring (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Inks, Pencil-Leads, Or Crayons (AREA)

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Publications (1)

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Citations (9)

• 1975
  • 1975-04-09 DE DE2515523A patent/DE2515523C3/de not_active Expired
  • 1975-12-16 US US05/641,252 patent/US4097510A/en not_active Expired - Lifetime
• 1976
  • 1976-04-02 NL NL7603465A patent/NL7603465A/xx not_active Application Discontinuation
  • 1976-04-06 BR BR7602069A patent/BR7602069A/pt unknown
  • 1976-04-06 CH CH431376A patent/CH602889A5/xx not_active IP Right Cessation
  • 1976-04-07 IT IT22067/76A patent/IT1058379B/it active
  • 1976-04-07 IN IN609/CAL/76A patent/IN144446B/en unknown
  • 1976-04-08 AR AR262819A patent/AR224855A1/es active
  • 1976-04-08 FR FR7610259A patent/FR2307021A1/fr active Granted
  • 1976-04-08 JP JP51038839A patent/JPS6043384B2/ja not_active Expired
  • 1976-04-08 AU AU12815/76A patent/AU1281576A/en not_active Expired
  • 1976-04-08 CA CA249,842A patent/CA1083590A/en not_active Expired
  • 1976-04-09 BE BE166028A patent/BE840599A/xx not_active IP Right Cessation
  • 1976-04-09 GB GB14651/76A patent/GB1505009A/en not_active Expired

Patent Citations (9)

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